942157-12-2Relevant articles and documents
SmI2-promoted radical addition reactions with N-(2-indolylacyl)oxazolidinones: Synthesis of bisindole compounds
Lindsay, Karl B.,Ferrando, Francese,Christensen, Kasper L.,Overgaard, Jacob,Roca, Tomas,Bennasar, M.-Lluisa,Skrydstrup, Troels
, p. 4181 - 4188 (2007)
(Chemical Equation Presented) The treatment of N-acyl oxazolidinones of N-benzyl 2-indolecarboxylic acids varying in the substitution pattern of the indole ring with samarium diiodi de at -78°C led to the formation of two indole dimer products. The major product isolated in yields from 55 to 59% represents an unsymmetrical dimer arising from 1,4-addition to the 2-indolecarboxylic acid derivative of a possible ketyl-type radical anion intermediate originating from the reduction of the exocyclic carbonyl group of the N-acyl oxazolidinone. The minor dimer, represented by a symmetrical diketone, was produced in yields ranging from 11 to 23%. Even in the presence of an α,β-unsaturated amide, dimerization was the preferred pathway rather than the formation of a γ-keto amide. Upon treatment with acid, the unsymmetrical indole dimer cyclized to form a diindolequinone. Finally, the N-acyl oxazolidinones of pyrrole-2-carboxylic acid and 3 indolecarboxylic acid preferred in both cases to undergo C-C bond formation with an acrylamide in the presence of SmI2 rather than dimerization.
